(S)-(-)-4-Isopropyl-2-Oxazolidinone For Synthesis

N2 - Dolastatin 10 (1), isolated from the sea hare Dolabella auricularia, has proved to be an exceptionally promising antineoplastic substance. Synthesis of this new and important peptide has been achieved. However, a more convenient and stereoselective synthesis of its three chiral center dolaproine (2a) unit has become necessary. A practical solution to this challenging problem was realized by employment of the following key reaction steps. Chiral oxazolidinone 5 was condensed at -75°C with S-prolinal 4 using dibutylboron triflate to direct the stereochemical course of the aldol reaction. Methylation of the product (6, 60-80% yields) and cleavage of the amide, in 83 and 93% yields respectively, completed a facile route to N-Boc-dolaproine (2b). Pertinent aspects of the aldol reaction and cleavage of oxazolidinone amides are discussed.

A Rapid Synthesis of 4-Oxazolidinones: Total Synthesis …
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The synthesis of all four individual isomers of 3-methyl-3-(2'-naphthyl)analine was accomplished using asymmetric conjugate 1,4-addition followed by direct or indirect azidation using an Evans-type chiral auxiliary (4-phenyl-2-oxazolidinone).


(R)-(+)-4-Benzyl-2-Oxazolidinone For Synthesis - …

(S)-(-)-4-Benzyl-2-Oxazolidinone For Synthesis | VWR
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(S)-(-)-4-Benzyl-2-oxazolidinone is used in chiral auxiliary asymmetric alkylation. It has been used in the synthesis of (S)-equol. Preparation and functionalization of chiral, stabilized ylides. It was used for asymmetric synthesis of (3R)- and (3S)-piperazic acid.


Staphylococcal Infections Medication: Antibiotics

AB - The synthesis of all four individual isomers of 3-methyl-3-(2'-naphthyl)analine was accomplished using asymmetric conjugate 1,4-addition followed by direct or indirect azidation using an Evans-type chiral auxiliary (4-phenyl-2-oxazolidinone).

Infection due to coagulase-negative staphylococci: …

The enantiomers and the cis isomers of two previously studied 4,5-disubstituted oxazolidinones have been synthesized, and their binding to the T-box riboswitch antiterminator model RNA has been investigated in detail. Characterization of ligand affinities and binding site localization indicates that there is little stereospecific discrimination for binding antiterminator RNA alone. This binding similarity between enantiomers is likely due to surface binding, which accommodates ligand conformations that result in comparable ligand-antiterminator contacts. These results have significant implications for T-box antiterminator-targeted drug discovery and, in general, for targeting other medicinally relevant RNA that do not present deep binding pockets.

Application of 4,5-O,N-oxazolidinone protected …

N2 - The synthesis of all four individual isomers of 3-methyl-3-(2'-naphthyl)analine was accomplished using asymmetric conjugate 1,4-addition followed by direct or indirect azidation using an Evans-type chiral auxiliary (4-phenyl-2-oxazolidinone).